This invention relates to novel acylamides of .beta.-X-ethenesulfonyl substituted aminoarenes, and to methods for controlling the growth of plant and animal organisms utilizing such materials.
As used herein, the references to the bioactive characteristics of the compounds of the present invention pertain to their use for killing or inhibiting the growth or functions of plant or animal organisms, e.g., microorganisms such as bacteria, fungi, protozoa or the like, or nematodes, snails, or other higher plant or animal systems.
Various ethenesulfonyl arenes have heretofore been proposed as useful bioactive compounds. Such materials include, for example, the amino and acylamidoarenesulfonyl-substituted acrylonitriles, acrylamides, acrylates and the like disclosed in copending Richter application Ser. No. 228,410 filed Feb. 22, 1972, now U.S. Pat. No. 3,821,399, owned by the assignee of the present invention. Methods for the preparation of compounds of the preceding types are disclosed, for example, in Richter and Tsolis U.S. Pat. No. 3,541,119 granted Nov. 17, 1970, also owned by the assignee of the present invention.
Beta-substituted ethene-aminoarenes of the above types find application as bactericides, fungicides, herbicides or the like. One material so useful is 3-(4-aminobenzenesulfonyl) acrylonitrile [or (2-cyanoethene)sulfonyl-4-aminobenzene]; this compound may be conveniently and economically prepared employing the technique described in the aforesaid Richter and Tsolis patent. While this material is a powerful bioactive substance, its use is undesirable for certain applications, the amino group reacting with many substances and the compound itself having a strong yellow color. Moreover, this and similar aminoarenes tend to be irritant to warm-blooded animals. As disclosed in the aforesaid application, various of the carboxylamido derivatives of the .beta.-X-ethenesulfonyl substituted aminoarenes are less reactive, less irritant, and generally have less intense colors than the corresponding aminoarenes themselves. These carboxamido compounds possess bioactivities equal to and, frequently, greater than those of the corresponding base aminoarenes.
It has now been discovered that other N-acylamido derivatives of .beta.-X-ethenesulfonyl-substituted aminoarenes, viz., various sulfonamido, sulfinamido, sulfenamido, phosphoramido, thiophosphoramido, phosphinamido, phosphonamido, and thiophosphonamido, derivatives thereof, may be utilized in the same manner as the carboxamido compounds as bioactive materials for controlling the growth of plant and animal organisms, while frequently also providing increased biological activity, lesser reactivity, better color and additional useful properties.